MLB Roundtable: Which team needs to win the World Series the most?

Opportunities to win the World Series don’t come along very often for the vast majority of Major League Baseball franchises. When they do, there’s always very little margin for error.

We’ve already seen this week how quickly the opportunity can slip away. The postseason dreams ended for the Chicago Cubs and Oakland Athletics. Both teams were eliminated in their respective league’s wild-card game. The Atlanta Braves and Colorado Rockies might follow right behind them after falling behind 0-2 in their respective NLDS.

For now, eight teams remain, and each is feeling a certain degree of urgency to make this their season. Yes, even the defending champion Houston Astros. However, for some of these teams, and more specifically some of these fanbases, it holds even more importance. For some, that’s because a World Series celebration hasn’t happened in a long, long time. For others, because it hasn’t happened ever.

What we’re trying to say is, winning it all is not easy. With that in mind, we’ve asked the Yahoo Sports crew which of the eight teams remaining in this year’s postseason need to win the World Series the most in 2018, and why.

Cleveland Indians

It’s the Indians for me. And yes, the 69-year championship drought is a big reason for that, but it’s also the shape of the current landscape. While the rest of the AL Central still has a lot of catching up to do, the Indians are definitely getting closer to their championship window closing. Even this season they’ve clearly taken a couple steps back, which is why they took the chance on Josh Donaldson. With some key free agents this winter, other AL powers getting stronger, and new teams getting ready to rise, this is the year the Indians need to bring the World Series championship back to Cleveland. (Mark Townsend)

While the Brewers and Rockies are the franchises without a World Series in this divisional round, neither are really the team most in need of a title. That would be Cleveland, who has a World Series drought longer than the existence of both of those teams. The team is currently on a run of three straight AL Central titles and doesn’t appear to be slowing down with José Ramírez, Francisco Lindor and a stacked rotation, but every year could be considered another missed opportunity at this point. (Jack Baer)

Boston Red Sox

Let’s forget history and droughts and just think about the now. The Boston Red Sox had their best season in franchise history. They won the most games in the regular season. They’ve spent the last few years either paying big bucks to free agents (J.D. Martinez and David Price) or making big trades to accelerate a championship (Chris Sale). If they don’t win a World Series, 2018 will be a gigantic failure. The Red Sox already seem to be doubted a little more than a 108-win team should be because of the holes in their bullpen. If they don’t win it all, their detractors will just have more ammo. (Mike Oz)

Los Angeles Dodgers

Most teams don’t see their windows for contention stay open this long. After coming so close the past couple seasons, the Dodgers need to find a way to break through soon. Once the season is over, the Dodgers could lose Manny Machado, Brian Dozier and Hyun-jin Ryu. Clayton Kershaw could opt out, and while everyone expects him to return to the Dodgers, there’s no guarantee he’ll stay healthy after failing to reach 200 innings over the past three seasons. On top of that, Rich Hill, Matt Kemp and Justin Turner are already in their mid-30s. (Chris Cwik)

The Los Angeles Dodgers have captured six consecutive NL West titles and have no World Series to show for it. Their last title win? 1988. At season’s end, the Dodgers will lose midseason trade acquisition Manny Machado and it is possible that ace Clayton Kershaw opts out of his contract as well. Superstars such as Justin Turner are only growing older and a repeat career year from Max Muncy is hardly in store for the future. The Dodgers have all the pressure in the world this October to finally win it all. (Johnny Flores)

Milwaukee Brewers

The Brewers have only existed since 1970 (or 1969 as the Seattle Pilots), and in all that time, they’ve only been to the playoffs four times before 2018. Four times in nearly 50 years! You can argue that a team that constantly whiffs in the playoffs, like the Washington Nationals, “needs” to win the World Series. But they at least make it to meaningful October baseball on a semi-regular basis. The Brewers have had so few appearances that every time they make it to October, it’s a franchise landmark. The Brewers winning would show everyone that small market teams can run with the big dogs, too. That there’s more than one way to rebuild a team, and it doesn’t have to look like the Yankees or Red Sox. With the American League so bereft of parity, a National League team like the Brewers winning would make a statement: a team doesn’t have to look or act like any other team to win it all. (Liz Roscher)

The Brewers are somehow still playing in the shadow of a Cubs team that’s already been knocked out. Forget the fact that they have some of the most thrilling players in the game right now in Christian Yelich and Josh Hader, a World Series win would take their rivalry with Chicago to a level we haven’t seen before. Milwaukee hasn’t even won a pennant in its history, so even just getting to the World Series would be a massive accomplishment. But a championship would make things just a little more interesting in the National League Central for years to come. With the Cubs and Cardinals struggling to find themselves, and the Reds and Pirates rebuilding as quickly as possible, this may be as wide open a window as Milwaukee ever gets. (Blake Schuster)

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